Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Mixing of two or more solid polymers; mixing of solid...
Reexamination Certificate
2001-09-25
2003-01-28
Dawson, Robert (Department: 1712)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Mixing of two or more solid polymers; mixing of solid...
C525S386000, C528S112000, C528S113000, C528S115000, C528S418000, C528S421000
Reexamination Certificate
active
06512057
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a resin composition useful for use in for example a powder paint or the like, and a cured material obtained by curing the resin composition.
DESCRIPTION OF THE BACKGROUND ART
A powder paint has been known as the paint containing no organic solvent. In recent years, the non-pollution property thereof has drawn attention from the respect of so-called environmental concerns such as air pollution. Hence, the amount of the powder paint to be used has increased year after year. Depending on the use, various polymer compounds have been used as the binder resin for use in a powder paint. Specifically, a powder paint comprising an acrylic copolymer with an epoxy group in blend with an aliphatic dicarboxylic acid is useful, particularly as a top coating, owing to the excellent transparency, hardness degree and weatherability of the coating obtained from the powder paint. However, for use as a top coating, high performance is required in terms of smoothness and various mechanical properties. The powder paint known so far, comprising an acrylic copolymer with an epoxy group in blend with dodecanedioic acid or sebacic acid, is not satisfactory in a practical sense, in view of those properties described above.
SUMMARY OF THE PRESENT INVENTION
The present invention provides resin compositions containing a vinyl copolymer with an epoxy group and a branched glutaric acid.
Additionally, the present invention provides powder paints containing the resin composition, and cured materials obtained by curing the resin composition.
DETAILED DESCRIPTION OF THE PRESENT INVENTION
The vinyl copolymer with an epoxy group (sometimes simply referred to as “copolymer” hereinafter) can be produced, for example, by a method comprising copolymerizing a vinyl monomer with an epoxy group (sometimes referred to as “vinyl monomer A” hereinafter) with one or more other vinyl monomers copolymerizable (sometimes referred to as “vinyl monomer B” hereinafter), or a method comprising modifying a vinyl copolymer without an epoxy group to introduce an epoxy group therein. The latter method specifically includes for example a method comprising first synthetically preparing a vinyl copolymer with an isocyanate group within the molecule and subsequently allowing glycidol to react with the resulting copolymer, and a method comprising copolymerization of a vinyl monomer with a glycerylcarbonate group within the molecule and subsequent decarboxylation of the resulting copolymer. Additionally, a copolymer, which is obtained by copolymerization between the vinyl monomer A and the vinyl monomer B, may be modified, if necessary. Among the methods described above, the method comprising copolymerization between the vinyl monomer A and the vinyl monomer B is a simple, preferable method (a copolymer which is obtained by copolymerization between the vinyl monomer A and the vinyl monomer B, or which is a modified product of the copolymer described above is sometimes referred to as “copolymer A” hereinafter).
The vinyl monomer A includes for example glycidyl esters of (meth)acrylic acid, such as glycidyl (meth)acrylate, &bgr;-methylglycidyl (meth)acrylate, and the like; allyl glycidyl ethers such as allyl glycidyl ether, and allyl methylglycidyl ether, and the like; and alicyclic epoxy group-containing vinyl monomers such as 3,4-epoxycyclohexyl acrylate, 3,4-epoxycyclohexyl methacrylate, and the like. Herein, the term (meth)acrylic acid means methacrylic acid or acrylic acid. The other (meth)acrylic acid derivatives have similar meanings.
The vinyl monomer B includes vinyl monomers copolymerizable with the vinyl monomer A described above, with no specific limitation, for example (meth)acrylic acid esters such as methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, cyclohexyl (meth)acrylate, benzyl (meth)acrylate, and the like; hydroxyl group-containing (meth)acrylates such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 3-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, polyethylene glycol mono(meth)acrylate, polypropylene glycol mono(meth)acrylate, and the like, or (meth)acrylates produced by adding &egr;-caprolactone to the various hydroxyl group-containing (meth)acrylates described above; carboxyl group-containing vinyl monomers such as (meth)acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, and the like, or mono- or diesters of the carboxyl group-containing vinyl monomers described above with a monoalkyl alcohol with one to 18 carbon atoms; amino group-containing amide type vinyl monomers such as N-dimethylaminoethyl(meth)acrylamide, N-diethylaminoethyl (meth) acrylamide, N-dimethylaminopropyl (meth)acrylamide, N-diethylaminopropyl (meth)acrylamide, and the like; dialkylaminoalkyl (meth)acrylates such as dimethylaminoethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, and the like; amino group-containing vinyl monomers such as tert-butylaminoethyl (meth)acrylate, tert-butylaminopropyl (meth)acrylate, aziridinylethyl (meth)acrylate, pyrrolidinylethyl (meth)acrylate, piperizinylethyl (meth)acrylate, and the like; &agr;-olefins such as ethylene, propylene, 1-butene, and the like; halogenated olefins such as vinyl chloride, vinylidene chloride, and the like; aromatic vinyl compounds such as styrene, &agr;-methylstyrene, vinyltoluene, and the like; hydrolyzable silyl group-containing vinyl monomers such as &ggr;-(meth)acryloyloxypropyltrimethoxysilane, &ggr;-(meth)acryloyloxypropyltriethoxysilane, &ggr;-(meth)acryloyloxypropylmethyldimethoxysilane, and the like; fluorine-containing &agr;-olefins such as vinyl fluoride, vinylidene fluoride, trifluoroethylene, tetrafluoroethylene, chlorotrifluoroethylene, bromotrifluoroethylene, pentafluoropropylene, hexafluoropropylene, and the like; perfluoroalkyl perfluorovinyl ethers or (per) fluoroalkyl vinyl ethers, such as trifluoromethyl trifluorovinyl ether, pentafluoroethyl trifluorovinyl ether, heptafluoropropyl trifluorovinyl ether, and the like, provided that the alkyl moiety in the perfluoroalkyl perfluorovinyl ethers or (per)fluoroalkyl vinyl ethers preferably contains one to 18 carbon atoms; aliphatic carboxylic acid vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate, vinyl isobutyrate, vinyl caproate, vinyl caprylate, vinyl caprate, vinyl laurate, branched C5-C20 aliphatic carboxylic acid vinyl esters, vinyl stearate, and the like; and vinyl esters of various carboxylic acid esters with a cyclic structure, such as vinyl cyclohexanecarboxylate, vinyl methylcyclohexanecarboxylate, vinyl benzoate, vinyl p-tert-butylbenzoate, and the like.
The amount of the vinyl monomer A to be used is preferably at 3 to 99.5% by weight, more preferably at 5 to 80% by weight, and still more preferably at 10 to 60% by weight to the total of the vinyl monomers used for the production of the copolymer A. When the amount of the vinyl monomer A to be used is at 3% by weight or more, the mechanical properties of the coating obtained from a resin composition are improved more.
For the production of the copolymer, a polymerization initiator, a chain transfer agent, or the like, may preferably be used, in the case that the vinyl monomer A and the vinyl monomer B are copolymerized.
Specific examples of the polymerization initiator include azo compounds such as 2,2′-azobisisobutyronitrile, 2,2′-azobis-2-methylbutyronitrile, 2,2′-azobis-2,4-dimethylvaleronitrile, 1,1′-azobis-1-cyclohexanecarbonitrile, dimethyl 2,2′-azobisisobutyrate, 4,4′-azobis-4-cyanovaleric acid, 2,2′-azobis(2-amidinopropene) dihydrochloride salt, 2-tert-butylazo-2-cyanopropane, 2,2′-azobis(2-methylpropionamide) dihydrate, 2,2′-azobis(2,4,4-trimethylpentane), and the like; peroxyesters such as tert-butyl peroxyneodecanoate, tert-butyl peroxypivalate, tert-butyl peroxy-2-ethylhexanoate, tert-butyl peroxyisobutyrate, tert-butyl peroxylaurate, tert-butyl peroxyisophthalate, tert-butyl peroxyacetate, ter
Goto Makoto
Konishi Shohei
Murata Shigeru
Murayama Toshikazu
Yamada Jun-ichi
Aylward D.
Dawson Robert
Fitzpatrick ,Cella, Harper & Scinto
Kyowa Yuka Co., Ltd.
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